Styrene → 2-Isoxazoline-3-carboxylic acid, 5-phenyl-, ethyl ester

HRID 1918522

Reaction equation

[N+:1]([CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6])([O-:3])=O.[CH2:10]=[CH:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.N12CCN(CC1)CC2>C(O)C>[C:12]1([CH:11]2[O:3][N:1]=[C:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH2:10]2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of ethyl 2-nitroacetate (0.96 mL; 8.70 mmol), styrene (0.5 mL; 4.35 mmol) and 1,4-diazabicyclo[2.2.2]octane (DABCO) (0.050 mg, 0.438 mmol) in ethanol (2 mL) was stirred at 80° C. for 60 hrs. The reaction mixture was concentrated under reduced pressure and purified by flash chromatography on silica gel (eluent 2 to 20% ethyl acetate in heptane) to afford ethyl 5-phenyl-4,5-dihydroisoxazole-3-carboxylate 0.234 g (25%).

Workup

concentrationThe reaction mixture was concentrated under reduced pressure
custompurified by flash chromatography on silica gel (eluent 2 to 20% ethyl acetate in heptane)

Sources & evidence

ORD record: ord-2c3e3405b30f4095ae292036b9cf1ecd
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08618138B2

Linked notes

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